1121-76-2Relevant articles and documents
New description of substituent effect on electronic spectra by means of substituent constants-VI. Ultraviolet spectra of 4-substituted pyridine N-oxides and blue shifted iodine bands of their EDA complexes with iodine
Uno, Bunji,Kano, Kenji,Kaida, Naoki,Kubota, Tanekazu
, p. 937 - 944 (1989)
Electronic spectra of 4-substituted pyridine N-oxides and their EDA complexes with iodine were studied.The substituent effect on the near u.v. 1A1 intramolecular CT bands of the N-oxides and on the blue shifted iodine bands caused by CT complex formation are discussed in terms of a general equation, theoretically derived in order to describe the substituent effect on electronic spectra by means of substituent constants.The results are quite successful and supported by semi-empirical SCFMO-Cl calculations.Based on the results mentioned above, the character of n-? type N-oxide-iodine CT complexes is also examined.The complex formation constants(log K) and pKa values of the N-oxides correlate especially well, indicating that the CT interaction mechanism cannot be neglected in proton addition reactions such as hydrogen bonding and pKa values.
A general synthesis of bis(o-azaheteroaryl)methane derivatives from N-oxides of azines and azoles
Szpunar, Magdalena,Loska, Rafa?
, p. 2133 - 2137 (2015)
A general method of preparation of derivatives of bis(o-azaheteroaryl)methanes from aromatic N-oxides is reported, the key step of which is a 1,3-dipolar cycloaddition between N-oxides of azines or azoles and in situ generated terminal difluoroalkenes containing an o-azaheteroaryl substituent at the double bond. Selected products were applied for the preparation of two novel unsymmetrical analogues of BODIPY fluorescent dyes, containing both an imidazole and a quinoline or isoquinoline unit.
Iodine/TBHP-Promoted One-Pot Deoxygenation and Direct 2-Sulfonylation of Quinoline N-Oxides with Sodium Sulfinates: Facile and Regioselective Synthesis of 2-Sulfonylquinolines
Sumunnee, Ladawan,Buathongjan, Chonchanok,Pimpasri, Chaleena,Yotphan, Sirilata
supporting information, p. 1025 - 1032 (2017/02/15)
A highly efficient iodine/TBHP-mediated one-pot deoxygenative and regioselective 2-sulfonylation of quinoline N-oxides with sodium sulfinate salts has been developed. This metal-, base-, and phosphorus-free protocol employs readily accessible and easy-to-handle reagents and can be conveniently carried out at room temperature under mild conditions, providing an alternative access to a series of 2-sulfonylquinolines and other related heteroaryl sulfone products in moderate-to-excellent yields within a short reaction time.
Highly efficient and selective phosphorylation of amino acid derivatives and polyols catalysed by 2-aryl-4-(dimethylamino)pyridine-N-oxides-towards kinase-like reactivity
Murray, James I.,Woscholski, Rudiger,Spivey, Alan C.
supporting information, p. 13608 - 13611 (2015/01/09)
The chemoselective phosphorylation of hydroxyl containing amino acid derivatives and polyols by phosphoryl chlorides catalyzed by 2-aryl-4-(dimethylamino)pyridine-N-oxides is described.
